Highly chemoselective hydrogenolysis of iodoarenes

被引:56
作者
Faucher, N [1 ]
Ambroise, Y [1 ]
Cintrat, JC [1 ]
Doris, E [1 ]
Pillon, F [1 ]
Rousseau, B [1 ]
机构
[1] CEA Saclay, Serv Mol Marquees, F-91191 Gif Sur Yvette, France
关键词
D O I
10.1021/jo0109669
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The catalytic hydrodehalogenation reaction using molecular hydrogen and Pd/C has been revisited. It is shown that the speed of removal of halogen increases with increasing electronegativity I < Br < Cl. Nevertheless, selective dehydrohalogenation in compounds containing other reducible functions can be achieved only with iodine and not with bromine or chlorine. Selective deiodination of iodobenzophenone could be accomplished without reducing the carbonyl group. Hydrogenolysis of azidoiodoaromatic compounds to the corresponding azido compounds is high yielding. This selectivity was exploited for the labeling of benzophenone- and azido-containing compounds by deuterium and tritium.
引用
收藏
页码:932 / 934
页数:3
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